


The Icing On the Cake

by TheSpaceCoyote



Category: Homestuck
Genre: Boys in dresses, Crossdressing, First Time, M/M
Language: English
Status: In-Progress
Published: 2012-03-03
Updated: 2012-03-03
Packaged: 2017-11-01 01:19:07
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,910
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/350391
Author URL: https://archiveofourown.org/users/TheSpaceCoyote/pseuds/TheSpaceCoyote
Summary: <blockquote class="userstuff">
              <p>"Bro must've known. He must have been plotting this the whole damn duration of John's visit. He had seen the way you two dodged around each other with stuttering statements of "no homo," the way that every touch that got too tender or too intimate was either brushed off as "ironic" or a "prank."</p><p>That's what made him hang the two dresses out there in the room. He knew you two would take the bait. You knew that he knew, and yet you hadn't let it stop you when you had proposed to John that this would be the ultimate gay chicken test."</p><p>In which Dave and John experiment in crossdressing.</p>
            </blockquote>





	The Icing On the Cake

**Author's Note:**

> Well, both Ahmerst and Gutennachte on tumblr have been dabbling in boys in dresses this week, and in one of the livestreams people said they wanted some more so....I did a lil with Dave and John <3 Enjoy!
> 
> (Also I love Dave kind of being terrible at sex, it's way cute)

 

 

 

"You done in there yet, Egbert?" You holler through the bathroom door, giving it a light backhanded rap. John's splutter comes amidst the audible sounds of rustling fabric and fumbled zippers, but you can still hear him.

"A-ah, almost! Jeez, give me a minute, Dave!"

You would chuckle, but your current situation impairs you from doing anything more than pulling a wry smile. You cross your legs and try not to think about it, but the _clack_ of the shoes you have on pulls you back to reality. As does the soft sheer feeling of your stockings rubbing against your calves. 

Your Gay Chicken Battle had just flamed into the Great War of Crossdressing which had claimed many casualties already. Namely, your sanity, your dignity, and your masculinity. And John's were surely mortally wounded and would perish despite the best efforts of the med team. There was no hope for them, not in the face of so many daunting frills and zippers and buttons and bits of lace.  

Bro must've known. He must have been plotting this the whole damn duration of John's visit. He had seen the way you two dodged around each other with stuttering statements of "no homo," the way that every touch that got too tender or too intimate was either brushed off as "ironic" or a "prank."

That's what made him hang the two dresses out there in the room. He knew you two would take the bait. You _knew_ that he knew, and yet you hadn't let it stop you when you had proposed to John that this would be the ultimate gay chicken test. You dared him to, and when he had dared you back you had shrugged it off like it was no big thing. And it _wasn't_ novel to you--Bro had had you try on one of his stupid dresses before back when you were younger and stupider and convinced of his lie that it would up your level of irony a millionfold.  

But trying on the dress in _front_ of John, and then seeing John in a dress in turn might end up being a little more than you'd bargained for. 

You palm your face, tersely rubbing the bridge of your nose. You really, _really_ hope Bro doesn't come by right now. Before when you'd worn his dresses you'd sworn it was only due to his coercion, or the promise of a lesser beatdown next time you strifed. If he saw you willingly dressing up like a virginal schoolgirl he would have a fucking field day and all your credibility would be crushed under the heel of a bright orange Mary Jane. 

Yeah, _orange_. Fuckin' orange. Bright sherbet orange plastered all over your body in the form of a frosted Jello mold dress, a pair of candy-striped stockings, peachy gloves--the whole fuckin enchilada. It feels like Bro has _branded_ you in his favorite shade of atomic-tangerine, and that only further adds to your humiliation.

"Dave?"

John's quiet voice sounds right next to your ear, like he's pressed right up against the door on the other side. You turn your head. 

"Yeah, bro? You all right over there?"

"Uhm." You hear him fumbling and fussing, shoes clacking against the tiles and you can practically see him nervously hopping from foot to foot in your mind's eye. 

"Yeah, I'm fine just, uhm. Uhh. I'm going to come out now, okay?"

"Sure, bro." 

You take a step back as the door swings open, revealing John standing awash in the mellow light of the bathroom. He's hugging himself and biting his lip and he looks super nervous, but you can't pay too much attention to all that. Because he's wearing the dress. And while you expected that you didn't expect him to look…well, you didn't expect to _like_ it. 

John looks like a damn cake in that dress--a TLC bride's dream, quintuple-tiered with baby blue icing crossed in lacy patterns at the bottom. It's like spun sugar, bubblegum cotton candy just _barely_ clinging to John's skinny frame. It's light-- _airy._ You suppose that it fits him like that. 

Even though you'd thought your Bro to be an utter shithead for baiting you two with these dresses, you could practically kiss him right now for blessing you with the image of John Egbert in a fetishized Cinderella ball gown. 

"John," you breathe, voice softer than you've ever heard it, "John just…Christ, man."

John whimpers and hides his face, shaking his head back and forth in dismay.

"Jesus, Dave! This is…so fucking embarrassing…" He groans. You can see his skin bright red and burning up between the fingers of his gloves and wow that material is pretty and dang you kind of want to touch it and _what the fuck are you thinking_. 

You're thinking about wanting to touch John and _no_ , damn it you put those feelings to rest. You'd dug up those feelings, pissed on them and then buried them again upside down. They were gone and desecrated so _what_ were they doing here, making you hot and bothered and wanting your best bro as more than just that.  

Even though the layers of your bloomers and the dress it's very obvious that your tenting. And it seems obvious to John as well, the way his eyes drift down to your nether regions. You swallow hard, hands balled into fists, trying to remain as stoic as you can with a boner poking through your dress. 

You can't do it.

You surge towards John and grab his wrist, pulling him forward to you and jamming your lips together. John whines in surprise and tries to pull away, but you've _got_ him, and after a moment his resistance seems to melt. 

Well. You weren't expecting that. Though considering 90% of what's happening today has come out of bumfuck nowhere, you're not sure whether that's much of a valid distinction. 

You start sinking to your knees, pulling John with you. He comes willingly, knees buckling and hitting the tile. He bends backwards as you gently push at his chest until he's laying spread eagle against the bathroom tile, dress fanning outwards from his hips like a puddle of frosting. 

"This," He opens and closes his mouth a few times, trying to find his voice, "This is okay, right?" His fingers tighten on the back of your neck and you crane forward, letting him bring you closer. His eyes keep moving around, flitting behind your shoulders and above your head as if he suspects Bro or his Dad (magically transporting from thousands of miles away) to walk in on your impromptu love nest. 

"No, dude," You simper, papping his cheek, "This is totally not okay. I definitely don't have the hots for my best bro even when he's in a goddamn ball gown, and that's why I'm definitely not going to do _this_." And then your hands are down at John's knees and you're pulling his thighs apart. 

The force with which you had spread John's legs had tore the tights along the seam right at the crotch and damn, that was practically an invitation. Flight traffic controllers waving you right into John Egbert's awaiting asshole. You pull down your bloomers and slowly wriggle yourself out, hard and ready for landing. You investigate the tiny lump in the pocket embroidered on the chest of your dress and are pleased to find its a small tube of lube. You don't want to think that Bro had _expected_ thiswhen he'd left out the dresses, but you're still internally singing his praises. 

You don't know all that much about sex with dudes, but you figure it's just like putting figure A into slot B with a little bit of lube to slick the way. Like fitting a piece of furniture together. Though John admittedly is a little bit more sexy than a flimsy Ikea chair. 

You cover your own dick with the gel and decide to wing it, grabbing John's hips and levering him up. He suddenly jerks and pushes himself up on his elbows but you're already pressing against him, trying to dig your cock into his body. 

"Ow, Dave, fuck--Dave, Dave stop!" He kicks out his heels, shoes grinding against the tile,  and pushes himself away from you, looking up at you like you're crazy. You try to grab him again and pull him onto your dick but he pushes a hand in your face. 

"What the fuck are you doing?" he cries, voice shrill and offended. You lift your hand off his hips and pull at his wrist, dislodging his fingers from your face. 

"Uh, didn't think that was really up to much debate here, Egbert. Thought I was gonna fuck you and all but maybe I'm getting some mixed messages. Would you rather have a nice massage? Or maybe you just wanted our dicks to shake hands and then go about their merry ways."

You cross your arms. You're not pouting, no way. You just wish he wouldn't be such a bitch about you doing what you _know_ he wants. 

John looks up at you, mouth agape. He tilts his head to the side and furrows his brows like concentrating, trying to look through your mind and unravel the tangle of Strider senses.  

"Dave, seriously? I would've thought…." John trails off, looking away, before bringing up his hands and making a scissoring motion.

"You gotta, y'know. With your hands down there first before you…yeah." His vague explanation doesn't really click with you at first, but then you get it and your mouth forms a silent "O" before you feel your cheeks light up with embarrassment. 

John has apparently watched a lot more gay porn then you have. Which would basically mean any gay porn at all, since you didn't really make a habit out of it. 

"All right." You breath deep, in and out, "All right."

You figure you should take off the gloves but, well, you've already fucked this up royally so far and if you make John wait you fear he's going to change his mind. So you dribble the lube onto your index and forefinger, rubbing them together until the silk of the gloves is soaked and sticking to your skin. 

You slowly ease your fingers into him and John "oohs" softly, arching his spine and causing more of his dress to spill off of his hips. 

"Oh God, dude that feels…that's so _weird_ …" he mumbles as you press in more and more. His hand scrambles for something to cling onto, but the smooth tile floor provides him with nothing so he just settled for throwing his hand over his face, one finger hooked into his lip. 

You can feel the slime of his insides through the fabric of your glove as your prepare him. You swallow, wondering if the silk rubbing up against him is uncomfortable at all but with his hand covering half of his face you can't really tell. At least the noises he's making seem to indicate that he likes it. 

After awhile you look up and you see that John has moved his finger from his lip and is now biting into the knuckle, and you're not sure if its from nerves or because it hurts. You gently rub his leg anyway, the fabric of your own gloves rubbing against his tights and creating a soft and silky friction. 


End file.
